Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | 4-Methylmorpholine | HCID 7972 | — |
| Reactant | Ethoxalyl chloride | HCID 20884 | — |
| Reactant | [6-[(4-Chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]methylamine | HCID 23114559 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | HCID 23114882 | HCID 23114882 | 76% |
Reaction Steps
To a dichloromethane (4 ml) solution of the [6-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]methylamine (30 mg, 0.0734 mmol) obtained in Example 63 were added N-methylmorpholine (10 μl, 0.0881 mmol) and ethyl chloroglyoxylate (9 μl, 0.0807 mmol) under ice cooling. The resulting mixture was stirred at room temperature for 1 hour. Water was added to the reaction mixture, followed by extraction with dichloromethane. The organic layer was then sequentially washed with a saturated aqueous solution of sodium bicarbonate and brine. The resulting organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel column chromatography. The fraction obtained from the hexane:ethyl acetate=3:2 eluate was concentrated under reduced pressure to give the title compound (28 mg, 0.0550 mmol, 76%) as a white powder.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07932271B2 |
|---|
| Source dataset | uspto-grants-2011_04 |
|---|
| ORD ID | ord-ee37076f0cb94a1e8384bbd78c80b6e4 |
|---|
| Source note | uspto-grants-2011_04 |
|---|